Trifluoroacetic acid → (S)-1-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)ethylamine

Participants

Reaction Steps

[(S)-1-(1-Benzyl-6-fluoro-1H-benzoimidazol-2-yl)ethyl]carbamic acid tert-butyl ester (0.88 g, 2.39 mmol) was dissolved in DCM (10 mL) and TFA (4 mL) was added dropwise. The pale green mixture was stirred at RT for 1 h, under an atmosphere of nitrogen. The resultant mixture was concentrated in vacuo and the residue passed down an Isolute® SCX-2 cartridge, eluting with DCM, MeOH and then 2M NH3 in MeOH solution to afford the title compound as a pale red gum (0.60 g, 93%). 1H NMR (CDCl3, 400 MHz): δ 7.69 (1H, dd, J=8.81, 4.80 Hz), 7.37-7.28 (3H, m), 7.09-7.95 (3H, m), 6.89 (1H, dd, J=8.75, 2.44 Hz), 5.54-5.34 (2H, m), 4.26 (1H, q, J=6.67 Hz), 1.54 (3H, d, J=6.61 Hz)

Provenance & Evidence